The 3 Year Job Search and How I Got Into TechFrom being jobless with no tech background to one of the hottest startups in the valley

The past 12-months have been eventful. Going into the Christmas period I suddenly found myself out of a job as it became clear that my time at DataFox was coming to an end, and I started thinking about what I wanted to do next. The New Space industry that SpaceX is enabling was fascinating, so I started hanging around at NASA Ames trying to learn as much as I can from a friend — who was just managed to successfully take over a spacecraft that NASA abandoned. With only a handful of companies to join and my lack of a physics background I tried to be as realistic as I can… But then Meerkat happened.

One week later I was unofficially part of the team, and on my second day needed to find the words to describe how amazing those two week have been now that live streaming was a thing in, Meerkat: 15 Days In.

The right place at the right time, 3 years in the making

I grew up in the Bay Area and attended Homestead High (where Steve Jobs and Wozniak went to school) and then De Anza College for 2 years (where the original Macintosh was unveiled). My first job out of UC Santa Barbara was auditing hedge funds and venture capital funds in San Francisco. I left after two years to join a startup in Huntington Beach and moved back to my parent’s house 3 months later.

Despite growing up in the heart of Silicon Valley I had no relation to the tech world and didn’t know anyone… So I spent most of 2013 just meeting people and working for free.

This was a difficult time. I had no money coming in, no company to add to my Twitter bio, and each day the gap on my LinkedIn was growing. There was doubt, but unlike my college degree or the CPA I got at age 20, it actually felt like I was picking up broadly applicable skills. Introductions I asked for became more relevant (as defined by proximity to Naval Ravikant, who I wanted to work for at AngelList) and I was even starting to offer my own introductions to people — the first sign that I was starting to have something of value to offer that was relevant.

Optimize for learning rather than earning.

When I cold emailed Bastiaan Janmaat the CEO of DataFox offering to help with whatever was needed, it wasn’t clear what that would be. It was just the founders working out of the old StartX office, and they were upfront that their first hires would be in engineering. This didn’t change anything because I wasn’t optimizing for getting paid, I just wanted to work on something FinTech related, with people that were smarter than me. People end up rising up or averaging down to the environment we spend the most time in, and I just saw it as incredible privilege to be around so many Stanford people (StartX is the Stanford affiliated accelerator).

As we were figuring out what I could help, with the company blog was mentioned, to which I instinctively blurted “You know I can write! Would that be helpful to the team?” (this was based on the 300 views my first and second Medium posts got cumulatively). As it turned out, creating content for the DataFox Blog was something they were willing to let me help with.

We decided to turn my notes from Naval’s YouTube video on the Current State of Startups into a more formal summary. Having recently bombarded Naval as he was getting into his Uber at a conference two weeks earlier, this was an opportunity to reconnect! So I emailed him a draft before publishing, and within a few days the post was seen by over 7,000 people. Suddenly the Video Notes Series on the DataFox Blog was a thing. Almost as an afterthought we found something that I could be contributing.

I was successfully executing on my strategy of adding value without asking for anything.

In December of 2013 things were starting to come together and I became more comfortable with what I was doing. I didn’t know what path I was on, but it felt like I was going in the right direction. I gained confidence in seeing the progress and being able to point to tangible things as evidence. It was a form of self-validation for all the doubt throughout the year, and I wanted to share it, so I did two things:

I wrote my third post on Medium on my experience meeting people, wanting to work for AngelList, and how much I learned from watching long YouTube videos of tech luminaries (Naval actually ended up reaching out after asking if I wanted to meet). Amazing.

Chris Sacca got me into tech.

While I don’t recommend sending that long of an email to someone who doesn’t quite know you… I do recommend that you read it, as it provides a lot of context for what got me into tech. It was a combination of seeing the value of Twitter within the short time span that I gave it chance, and being exposed to the tech world as a possible avenue when the learning curve of hedge fund accounting was quickly coming to an end (cash & investments is literally the shortest balance sheet you’ll ever see, and the valuation of public companies is not very subjective).

If you’re just reading the highlighted part of the email: when Chris Sacca favorited my tweet about Uber in 2012 it showed me the power of Twitter and how it can be used to connect with people you wouldn’t normally get the chance to meet.

Explain.

Twitter is the where I was able to learn from, interact with, and eventually form all the relationships I owe everything to today. It is the reason I now feel like a part of the tech industry, and I’m not sure I would have stayed long enough to see the value of it if it wasn’t for that fav from Sacca in 2012. The only reason I was playing around with it again in the first place was because I was working on Lowercase Capital (my first VC client at RK) and Twitter was the most recognizable investment, so I wanted to get it. It’s similar to how I think about Pinterest today: it’s great, I have it, would love to understand it, but there’s nothing to act as a catalyst to show me what I could get out of it.

The catalyst to actively using Twitter toward the end of 2012

My first Twitter catalyst was when a conversation with a colleague about tweeting turned into “aren’t you on Sacca’s fund? He’s kind of a big deal…” which I didn’t know at the time. And when we looked him up, my perception of Lowercase changed. It went from being that VC fund I’m filling in for that doesn’t have a fancy hedge fund office space (in fact, no office) and only three people (a “Matt Mazzeo” just joined :tada:), to the fund with the high profile person that I might get a chance to talk during the client engagement.

The second catalyst was after my first Uber ride.The convenience was like magic. I wanted to tell people about it who could relate, but none of my friends or co-workers have used it, so I tweeted @travisk and @sacca instead (with no expectation that it would be read). Not only was it read, but I got an email from Twitter that said it was favorited.

Totally unexpected. I promptly took a screenshot and when I got back to the office, I must have mentioned it at least ten times throughout the day. Favorites being common, or as a way of showing that a tweet was read (as Chris uses them) wasn’t something I was aware of. To me, it was direct contact with someone I normally wouldn’t get a chance to interact with, AND my tweet was even a “favorite.”

This may all seem pretty embarrassing to admit… Except that (if you were reading the email closely) I kind of topped myself by emailingthe screenshotto Chris a year later.

The importance of having role models.

I remember going through my first year and loving every minute of it, yet never planned on staying much beyond the year of work experience I needed to get the CPA. The career path in public accounting ranges from making partner, going to Big 4 (where I was an intern and RK was acquired by KPMG after I left anyway) or going to industry — and I thought the prospect of joining a VC/PE/or hedge fund client was excellent. Very few people leave public accounting to do something completely different, and if you have a CPA it’s virtually unheard of; so there really needed to be something to get me to see outside of that mindset.

Inspiring stories with a hint of something to relate to can leave a lasting effect.

That initial spark was watching Chris’s PandoMonthly Fireside Chat with Sarah Lacy. His background prior to Google is crazy, and the way he went on to become one of the largest investors in Twitter is legendary. Then there was Uber — which is where the spark happened. After sitting in on a valuation call with Chris accounting no longer made sense, for me.

It’s important to revisit what you’re doing every few months and decide if it’s still the right thing right now, six months from now, and two to three years ahead. Anything longer and it’s too far out to be relevant. Failing to constantly reassess could mean following a map perfectly, but going to the wrong place.

Think about where you want to be two to three years ahead.

Finding someone who is doing now what you want to be doing in two to three years is an excellent point of reference. You’ll notice I mentioned Adam Besvinick in the initial email to Chris. Adam is now a VC at Deep Fork Capital, but used to intern for Chris at Lowercase. He is also the first person that took the time to meet with me when I was first starting out, and reading his post about transitioning from Finance to Tech left quite an impression. Super impressive story, and just within reach on the scale of somehow doable, to not a chance. It provided the motivation to reach out to more people and learn rather than instantly joining whatever would pay.

Adding value without expecting anything.

Chris would repeat that quote in interviews often — it stuck. I follow it every step of the way. Naval recently said a similar thing which expands on that mindset perfectly:

Eventually this led to finding out about an app called Popcorn Chat (based on a tweet from @Besvinick) and offered to help. The founder and I were wondering what this Product Hunt thing was that Popcorn was on (one of the first products to be hunted) which led to me emailing the founder himself, but for asking if he’d get on a call to chat about a couple of Popcorn features that I came up with. For some reason, Ryan Hoover accepted.

When I was putting together the recap from Sacca’s Product Hunt Live a few weeks ago it made me reflect on this new role I ended up in. It’s great, and fits what I want to do all too well. When I announced that I was joining the Product Hunt team the reaction and the number of people who reached out was humbling. It no longer felt like I was trying to break in to tech.

If you’ve read this far, amazing, hopefully some of it was useful (or entertaining). If so, please recommend :-) and remember that as long as we feel embarrassed by our naiveté every six months then we’re living outside of our comfort zone enough to learn and improve everyday.

This article was originally published on Medium and has been republished here with the author’s permission

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